Boron trifluoride etherate → HCID 86600676, compound

Participants

Reaction Steps

A solution of 0.48 g (approx. 88% pure) 1-(2,3,4,6-tetra-O-benzyl-1-hydroxy-D-glucopyranosyl)-3-[4-(tert-butyl-dimethyl-silyloxy)-benzyl]-4-methyl-benzene in 3.5 ml dry acetonitrile is cooled to −40° C. under argon. 0.13 ml triisopropylsilane and 0.08 ml boron trifluoride etherate are added dropwise to the cooled solution. The solution is stirred for 3 h at −35° C., before another 0.02 ml of triisopropylsilane and 0.01 ml of boron trifluoride etherate are added. After a further 2 h at −40° C. aqueous potassium carbonate is added and the solution is stirred for 1 h at ambient temperature. Then it is diluted with water and extracted four times with ethyl acetate. The organic phase is dried over sodium sulphate, concentrated and chromatographed through silica gel (cyclohexane/ethyl acetate 10:1->4:1).

Provenance & Evidence